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Synthesis and Opto-Electrical Properties of Novel Conjugated Small Molecule Bearing a B←N Moiety
Macromolecular Research ( IF 2.4 ) Pub Date : 2020-06-26 , DOI: 10.1007/s13233-020-8113-1
Ka Yeon Ryu , Dan-Bi Sung , Yong-Ju Kwon , Hyun Yeong Kim , Chongmok Lee , Won-Suk Kim , Kyungkon Kim

Effects of the B←N unit on the energy level of conjugated small molecule were investigated by synthesizing a new small molecule BPDPP (3,8-bis(5-(2,5-dioctyl-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)-thiophen-2-yl)-6,6-dioctyl-6H-benzo[3,4] [1,2]azaborolo[1,5-a]pyridin-5-ium-6-uide) via Suzuki coupling. For comparison, CPDPP (6,6′-(5,5′-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-dioctyl-3-(thiophen-2-yl)pyrrolo[3,4-c] pyrrole-1,4(2H,5H)-dione)) having the same chemical structure with BPDPP except the B←N unit is synthesized through the same coupling reaction. Absorption spectra and cyclovoltammetry analysis for these small molecules revealed that the B←N unit reduces the band gap of BPDPP by maintaining large oxidation potential. As a result, the blend film of BPDPP and PC71BM maintained 87.4% of the initial absorption intensity after 1sun light soaking test for 315 h. The photo stability of the BPDPP is significantly higher than the blend film of P3HT: PC71BM, which maintained only 19.8% of the initial absorption intensity only after light soaking for 23 h.



中文翻译:

具有B←N部分的新型共轭小分子的合成及光电性能

通过合成新的小分子BPDPP(3,8-bis(5-(2,5- dioctyl -3,6-dioxo-4-(thiophen))来研究B←N单元对共轭小分子能级的影响-2-基)-2,3,5,6-四氢吡咯并[3,4-c]吡咯-1-基)-噻吩-2-基)-6,6-二辛基-6H-苯并[3,4]通过铃木偶联的[1,2]氮杂硼杂环[[1,5-a]吡啶基-5-基-6-脲)。为了比较,CPDPP(6,6'-(5,5'-(9,9-二辛基-9H-芴-2,7-二基)双(噻吩-5,2-二基))双(2,5-与BPDPP具有相同化学结构的二辛基-3-(噻吩-2-基)吡咯并[3,4-c]吡咯-1,4(2H,5H)-二酮))除了B←N单元是通过相同的偶联反应合成的。这些小分子的吸收光谱和循环伏安分析表明,B←N单元通过保持较大的氧化电位来减小BPDPP的带隙。结果,BPDPP和PC 71 BM的共混膜在1个日光浸泡测试315小时后仍保持了初始吸收强度的87.4%。BPDPP的光稳定性明显高于P3HT:PC 71 BM的共混膜,后者仅在光浸泡23 h后才保持初始吸收强度的19.8%。

更新日期:2020-06-26
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